Sailing America opens up wide and varied cruising grounds, taking in the Pacific and Atlantic oceans, as well as temperate and tropical locations to explore under sail. Steve Walburn shares his 10 best spots

Sailing America: 10 of the best spots to cruise in the US

From the Pacific and Atlantic oceans to the Gulf of Mexico, America boasts the world’s eighth-longest coastline.

Throw in an abundance of freshwater sailing in the Great Lakes, along with myriad tropical destinations accessible from US waters, and the United States presents nearly endless cruising opportunities for visiting sailors.

A yacht with a coloured sail cruising past Chicago Automated lighthouse on Lake Michigan while cruising america

Lake Michigan, one of the five Great Lakes, offers plenty of sailing, including Chicago Harbor, guarded by the automated lighthouse on the northern breakwater. Credit: Getty

Whether you sail across the Atlantic or fly to the States and charter a boat, UK cruisers will find sailing adventure as varied as the country itself.

With both major coastlines stretching north and south, there is always year-round cruising at one latitude or another.

Starting in the Northeast during summer and working clockwise around the country, here are ten great destinations to set sail in the New World and beyond.

Penobscot Bay, Maine

Sailing America - a large double masted wooden sailing yacht cruises past a lighthouse at Casco Bay

Maine has a strong boat building heritage and you will see plenty of examples as you cruise the bay, including Casco. Credit: Getty

With its craggy coastline and rich maritime heritage, Maine may be the ultimate US cruising ground.

From Casco Bay in the south to the Bay of Fundy in the north, a labyrinth of wilderness islands, picturesque villages, and secluded anchorages await adventurous mariners.

Roughly in the middle of that ragged coast are the celebrated waters of Penobscot Bay.

There Maine’s tradition of wooden boat building thrives in places like Brooklin Boat Yard and Center Harbor.

Pink granite outcrops and evergreen forests line the scenic coast.

Gunkhole in a private cove for a day or two, then grab a mooring ball or a slip in any of dozens of Penobscot Bay harbors.

Excellent hiking and camping await on islands such as Warren Island State Park, where in summer the lush maritime woodlands are ripe with wild blueberry and raspberries.

Sailing America: Getting to Penobscot Bay, Maine

Peak Maine cruising season is July through August. During that time, the prevailing wind is a light southerly of about 5 knots.

The bay’s 20-mile breadth poses little difficulty entering either west or east Penobscot Bay.

However, a big tidal range, frequent fog, and a gauntlet of lobster pots make for challenging sailing.

Granite headlands call for vigilance against underwater ledges and obstructions.

Provisioning opportunities can be limited, so stock up in ports such as Rockland or Camden before venturing out.

Bareboat charters are available through Johanson Boatworks in Rockland ( and Northpoint Yacht Charters in Rockport (

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Sailing America: Newport, Rhode Island

Sailing America - an aerial view of Newport Harbour in Rhode Island, with boats anchored in the bay

The harbour at Newport is usually crowded but there are plenty of places to anchor in the bay. Credit: Getty

Newport, Rhode Island, is arguably the capital of US sailing. Nautical influences on this classic New England town range from the world’s largest fleet of 12 Metres to the Golden Age of Sail.

Consistent winds in relatively protected Narragansett Bay make for pleasant sailing in a light chop. The local climate is warmed by proximity to the Gulf Stream, and the sailing season can run through October.

Downtown Newport offers world-class dining, haul-out and repair facilities, and a bustling city centre full of diverse American architecture.

The Herreshoff Marine Museum and America’s Cup Hall of Fame are in nearby Bristol, and the famed Newport International Boat Show is in September.

Just outside Narragansett Bay lie the famed cruising grounds of Martha’s Vineyard, Nantucket, and Block Island, all within a day’s sail.

The entrance to Long Island Sound (and New York Harbor via the East River) is about 40 miles south.

Sailing America: Getting to Newport

Narragansett Bay is divided into three sections: West Passage, East Passage, and the Sakonnet River. Conanicut Island lies in the middle and offers shelter on either side during strong southerly or northeasterly blows.

There are various mooring fields in all three sections of the bay, with popular anchorages off the east shore of Aquidneck Island.

Upon entering the bay from Rhode Island Sound, Newport Harbor is just beyond a relatively narrow channel south of Castle Hill Lighthouse at the mouth of East Passage.

The water widens inside, with plenty of room to maneuver until you enter the harbor proper, which is usually crowded with moored vessels.

Sail in a 12 Metre regatta with

Bareboat in Narragansett Bay through

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Sailing America: Chesapeake Bay

Chesapeake Bay from the air showing the harbour and boats. It is one of the best spots for those wanting to go sailing America

Spring and fall are the best times to cruise Chesapeake Bay. Credit: Getty

Chesapeake Bay is the largest inlet on the Atlantic Coast.

Its massive watershed drains six states and the District of Columbia, but the saltwater ecosystem is confined primarily to Virginia and Maryland.

With more total shoreline than the entire US west coast, scores of major cities and small towns line the bay.

The upper reaches are highlighted by Annapolis, Maryland, famous for its sailing heritage and annual boat show.

Baltimore Harbor is a little farther north, and Washington DC is just to the west on the Potomac River.

In contrast to the west side of the bay, the Eastern Shore is mostly farmland, with endless creeks, bays, and narrows offering a gunkholer’s delight.

Popular small ports on the eastern side include St. Michaels on the Miles River and Oxford on the Tred Avon River.

The southern bay is home to busy Virginia ports such as Virginia Beach and Norfolk, the site of a huge US naval station.

Sailing America: Getting to Chesapeake Bay

Offshore sailors enter the bay at the 17-mile-long Chesapeake Bay Bridge-Tunnel connecting mainland Virginia Beach to the Eastern Shore.

For inshore travellers, the Atlantic Intracoastal Waterway joins the bay with protected North Carolina waters farther south.

The Chesapeake and Delaware Canal connects the upper Chesapeake Bay to Delaware Bay. Both stretches are important ICW corridors for snowbird cruisers migrating with the seasons.

Mid-summer brings stifling heat and humidity, but spring and fall offer pleasant sailing in temperate climates.

Bareboat rentals with Waypoints Annapolis (

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Beaufort to Beaufort, The Carolinas

Beaufort, North Carolina. A cruising yacht sails pass a superyacht while sailing America

Beaufort, North Carolina is a good base for exploring the Outer Banks to the north

A cruise from Beaufort, North Carolina, to Beaufort, South Carolina, features the historic ports of both cities, as well as the antebellum city of Charleston, SC.

On the northern end lies Beaufort, NC (pronounced Bō-fert), with its quaint waterfront, maritime history museum, and quick access to the wild Outer Banks.

Beaufort’s immediate neighborhood includes the pristine Rachel Carson marine reserve, Shackleford Banks and its herd of wild horses, and Cape Lookout National Seashore, the southern terminus of one of the longest undeveloped coastlines on the Atlantic seaboard.

South Carolina’s identically named town (pronounced Bū-ferd) is home to classic Lowcountry marshes graced with vibrant green spartina grasses and an afternoon light that is downright ethereal.

In between lies Charleston, a sprawling seaport of historic antebellum homes, world-class restaurants, and graceful southern charm.

Sailing America: Getting to Beaufort to Beaufort

It is roughly 350 miles between the Beauforts, which can also include stops at salty towns like Wilmington, NC, and Myrtle Beach, SC. Well-travelled sections of the ICW connect all three cities.

Extra caution is advised when entering or exiting any of the inlets that bisect the mid-Atlantic barrier islands, especially on strong southeasterly winds or at low tide.

Frying Pan Shoals off the cape at Bald Head Island extends well offshore and deserves a very wide berth.

Transient boat slips are available in all three harbours through Safe Harbor Marinas (

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Florida Keys

Yachts anchored at a palm covered Wisteria Island in Key West

There are hundreds of islands to cruise in the Florida Keys including Wisteria Island in Key West. Credit: Getty

The Florida Keys are often perceived as simply a jumping-off point for passage to the Caribbean, but they offer excellent cruising in themselves.

Charter a boat in Miami, and you have more than 800 islands and islets stretching 150 miles from Key Biscayne to Key West.

Beyond that lie the Marquesas and Dry Tortugas island groups, both US territories and the centrepieces of a US national wildlife refuge and a national park.

The 70-mile passage from Key West to Dry Tortugas is a popular trip accessible to most intermediate-level cruisers.

The Keys are also home to the only barrier coral reef in North America, and the third largest in the world.

Ashore any of the Keys you will find a kitschy, flip-flop vibe unlike anywhere else in the States. And best of all, the Keys are indeed a great staging area for any itinerary that takes you deeper into the Caribbean.

Sailing America: Getting to the Florida Keys

Most marine areas from Key Biscayne to the Dry Tortugas are protected by the 3,800-square mile Florida Keys National Marine Sanctuary.

There are mooring balls located up and down the reef. Contact the sanctuary for a free map of mooring ball locations (

If anchoring, keep in mind that much of the Keys is marl bottom, which can make getting a good anchor set difficult.

When in doubt, use the clear waters to dive on your anchor. Bareboat charters are available through Miami Yacht Charters (

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Continues below…

One of the delights of sailing Mexico - A national park, Isla Isabel, 15 miles off the west coast of Mexico, is a major breeding area for frigate birds, brown and blue-footed boobies

Sailing Mexico: a fiesta afloat

Sailing Mexico was the start of Joshua Shankle and Rachel Moore's plan to circumnavigate the world. They find bustle and…

US Virgin Islands

Sailing America - the USVI offer many cruising grounds. A couple on the deck of a yacht sunbathing while anchored

St John is a popular sailing destination in the USVIs, but you can find a quiet anchorage, off Hawksnest Bay. Credit: Getty

The US Virgin Islands (USVI) offer classic cruising in cerulean water against a backdrop of green volcanic islands.

Distinct from the flatter and more arid Bahamas to the north, the USVI is a tropical paradise lying at the dividing line between the Atlantic Ocean and the Caribbean Sea.

In addition to the group’s three main islands, there are scores of smaller islets and cays scattered throughout the archipelago.

They are renowned for sandy white beaches and lush tropical forests. Maho Bay on St. John is one of the more popular destinations, known for the opportunity to snorkel with green and hawksbill sea turtles.

There are numerous national parks, monuments, and marine preserves throughout the islands. More than half of St. Thomas is a US national park.

Point your bow toward the USVI, and you will end up at the centre point of the entire Virgin Islands archipelago, with the British VI lying due east and the lesser-known Puerto Rican VI to the west.

Sailing America: Getting to the US Virgin Islands

There are several ways to sail to the Virgin Islands. A rhumb line from the US mainland at Miami is known as the Thorny Path due to the labyrinth of islands, reefs, shoals, currents, and upwind slogs complicating the route.

This nearshore passage is best handled in short hops over a long period of successive weather windows. That means taking several weeks instead of days.

The alternative is known as the I-65 Expressway, so named because it takes you east of Florida offshore to longitude 65°W.

From there you sail south across the trades in true offshore conditions. Or you can just fly into St. Thomas and charter with Waypoints USVI (

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Channel Islands, California

Yacts mooring at Avalon harbor at Catalina island

All moorings at Avalon harbor on Catalina, one of the Channel Islands, are allocated on a first-come, first, serve basis. Visiting yachts should stand by the harbor entrance to be assigned a mooring. Credit: Getty

California’s Channel Islands consist of eight major islands divided into a northern group and a southern group.

Cruisers visiting southern California will find either destination a short sail off the mainland.

Characterised by arid, rugged terrain and abundant wildlife, this pristine area presents challenging sailing that rewards mariners with stunning scenery in remote anchorages.

A menagerie of whale, dolphin, sea lion, and seal species inhabit these waters, most of which are encompassed in the Channel Islands National Marine Sanctuary.

Onshore you will find scattered beaches, sea caves, and excellent hiking in places such as the Pelican Bay Trail on Santa Cruz Island. Flora and fauna range from cacti to buffalo.

Because much of the Channel Islands are protected or private, you may need a permit to go ashore.

When you are ready to regroup in port, check out the scenic town of Avalon on Catalina Island.

At a population of only 3,460, it is the most developed town in these otherwise pristine islands and a great place to re-provision, shop, or dine out for a night or two.

Sailing America: Getting to the Channel Islands

The closest of the Channel Islands is less than 15 miles from the mainland, but the entire archipelago is known for ocean swell, confused seas, and strong winds.

To the north, Point Conception is sometimes referred to as the “Cape Horn of the Pacific” due to frequent gales that threaten seas in the northern group.

And the downslope Santa Ana “Devil Winds” blowing offshore from the mainland are a force to be closely monitored

All the islands offer plenty of anchorages, but relatively few are fully protected.

Perfect your anchoring technique and ground tackle before setting sail to the Channel Islands.

Charter or bareboat from Santa Barbara Sailing Center (

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San Francisco Bay, California

Yachts sailing under the Golden Gate Bridge under a blue sky

It is best to sail under the Golden Gate Bridge on the slack before the flood. Credit: Getty

When you have had your fill of California’s wild coastal islands, head north for some urban cruising in beautiful San Francisco Bay.

Sailing under the Golden Gate Bridge is a milestone for any mariner.

Host of the 2013 America’s Cup, the bay is a colourful mix of cityscape and nature, from local green spaces to surrounding recreation areas, parks, and mountains.

Hip and progressive, America’s iconic west coast city reflects cultural influences ranging from the Beat Generation to nearby Silicon Valley.

At the nautical epicentre are Aquatic Park, Fisherman’s Wharf, and the San Francisco Maritime National Historical Park, including its flagship Balclutha, a 301-foot square-rigger built in 1886.

Take a couple of days or a couple of weeks to cruise past the exhilarating port cities lining the bay, and you’ll find plenty of sightseeing—and wind—to keep any sailor entertained.

Sailing America: Getting to San Francisco Bay

Most cruisers chart a counterclockwise route through the bay, always mindful of the powerful winds running through the narrows under Golden Gate Bridge, a long fetch known as The Slot.

Notorious for fog and chill ocean winds, even in the peak of summer bay sailing is a bracing experience.

Major shipping lanes, stacked seas, and strong currents add to the challenge (and accomplishment) of sailing in San Francisco Bay.

Some of the more popular anchorages include Clipper Cove, Richardson Bay off of Sausalito, Ayala Cove at Angel Island State Park, and Aquatic Park Cove on the northern edge of the city.

Bareboat or skippered charters are available through Spinnaker Sailing (

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San Juan Islands, Washington

Cruising America: yachts anchored at an orange red sunset in the San Juan islands

Lummi in the San Juan Islands offers a sheltered anchorage, with a view of Mount Baker, an active volcano. Credit: Getty

What Maine sailing is to America’s northeast coast, the San Juan Islands are to its Pacific Northwest.

This archipelago of temperate rainforests scattered between Washington State and Vancouver Island, British Columbia, offers some of the best cruising in North America.

Situated above the Strait of Juan de Fuca in the Salish Sea, the islands also mark a starting point for passages farther north along the magnificent BC coast and up the Inside Passage to Southeast Alaska.

The San Juans are former British territory charted in 1792 by Royal Navy officer George Vancouver, after whom many of the region’s most prominent landmarks are named.

Today, the islands are a serene outpost of sparse human inhabitation coexisting with towering fir and hemlock trees, black-tailed deer, sea otters, shorebirds, migrating waterfowl, and America’s highest concentration of its national symbol, the bald eagle.

Pods of resident orcas roam the myriad passes and inlets in pursuit of salmon and seals.

Cruisers needing to stretch their legs ashore will find pebble beaches and excellent hiking on nearly every island.

Sailing America: Getting to the San Juan Islands

You can spend a week and see plenty of the San Juans or spend years and still not see it all.

These compact islands are a labyrinth of passages, coves, and bays that make for world-class anchorages.

There are 11 Washington state marine parks in the San Juans, all of which offer moorings, campsites, and other essential facilities.

Underwater rocks and strong tidal flows abound, so large-detail charts and tide tables are a must. Shore-tying skills are also critical in anchorages that are too confined to permit standard anchoring.

Charters are available from San Juan Sailing (

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Hawaiian Islands

Yachts anchored a Kauai in Hawaiian islands; a rainbow is over the anchorage and the rich green hills can be seen in the distance

Yachts can only stay 72 hours in a single anchorage before moving on in Hanalei Harbor on Kauai, and the rest of the Hawaiian Islands. Credit: Getty

Although Hawaii is more than 2,000 miles from the American mainland, no US cruising guide would be complete without a nod to this storied Pacific destination.

Surrounded by steady trade winds, Hawaii offers year-round sailing in azure waters against a backdrop of lush volcanic islands.

Cruising sailors share the waters with humpback whales, spinner dolphins, monk seals, manta rays, green turtles, and a kaleidoscope of reef fishes.

Onshore, these isolated islands present a spectrum of micro-climates determined by altitude, wind, topography, and weather patterns.

The result is a rich diversity of ecosystems ranging from tropical forests to desertscape and alpine slopes.

The state is also among America’s most culturally diverse because of its central location between North America and East Asia. Its state flag still incorporates the Union Jack.

Sailing America: Getting to the Hawaiian Islands

The trade winds in Hawaii average about 15 knots from the east. However, wind accelerating through the passes between islands can make things very spicy.

The leeward or western side of the archipelago offers calmer seas most of the time.

Sailors depart for the Hawaiian Islands from all corners of the Pacific, including Mexico, Australia, New Zealand, and Alaska.

And, of course, you can always sail across from the US mainland. But that is a whole other story!

Bareboat options are limited in Hawaii due to the challenging conditions.

For a skippered charter, check out Yacht Charters Hawaii ( or Honolulu Sailing Company (

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Sailing America: Hidden Attractions

Museum Hopping

Herreshoff Marine Museum's Hall of Fame is a must visit. Credit: Getty

Herreshoff Marine Museum’s Hall of Fame is a must visit. Credit: Getty

Herreshoff Marine Museum and America’s Cup Hall of Fame

Brothers Nathanael and Francis Herreshoff are America’s most celebrated naval architects.

They built everything from canoes to torpedo boats but are best remembered as the authors of hundreds of sailing designs, five of which won America’s Cup titles.

Located in Bristol, RI, the museum is easily visited during a cruise of Narragansett Bay.

Chesapeake Bay Maritime Museum

Immerse yourself in Chesapeake Bay’s nautical history by sailing to St. Michaels, Maryland.

The local maritime museum consists of 35 buildings and 85 vessels, including the last working log-bottom bugeye, Edna Lockwood, a Chesapeake Bay oyster dredger declared a National Historic Landmark in 1994.

North Carolina Maritime Museums

This network of state history museums is dedicated to the story of North Carolina’s rich nautical history.

One of the best in the system is in Beaufort, NC, where you will find colorful exhibits of maritime history ranging from pirate ships to wooden skiffs.

San Francisco Maritime National Historic Park

Encompassing 50 acres, this US National Park Service facility is one of the west coast’s most important nautical history centres.

Among other attractions, it includes a museum, a fleet of six historic vessels, and a research centre housing thousands of photographs, articles, books, artwork, and naval drawings.

Bonus Cruising Grounds

The lighthouse on the Sanibel Island

Sanibel Island is a good place to stop for cruisers sailing up and down the Intracoastal Waterway, with direct access to the Gulf of Mexico. Credit: Getty

The Great Lakes

Straddling the US and Canadian border, the world’s largest group of inland lakes presents myriad freshwater cruising opportunities.

There is even access from the Great Lakes to the Atlantic Ocean via the St. Lawrence Seaway.

The grandaddy of them all, Lake Superior, offers stellar freshwater sailing around Isle Royale National Park, The Apostle Islands, and St. Ignace Island (in Canadian waters).

Gulf of Mexico

Oil and gas development and a relatively homogenous coastline tend to steer cruisers away from the Gulf of Mexico.

Yet America’s best white-sand beaches are found along the Gulf Coast. If you are cruising the tip of Florida, consider tucking around to its southwest side.

There you will find shallow-water cruising along the edge of Everglades National Park, 10,000 Islands National Wildlife Refuge, and the sugar-white beaches of Sanibel Island, Captiva, and Pine Island Sound.

Sailing America: What you need to know

A visa and a red passport

Credit: Getty

All temporary visitors to the US are required to have a passport, but not necessarily a visa.

Visit the US State Department website (Travel.State.Gov) and search ‘Visa Waiver Program’ for a list of participating countries.

Whether you clear in at the helm of your own vessel or plan to charter for a few days or weeks, here are some additional tips to keep in mind.

Clearing In

Cruising sailors must clear in at an official port of entry. A list of ports is available on the U.S. Customs and Border Protection website (

Arriving sailors should have the standard portfolio of passport and visa (if required), boat registration, insurance documentation, crew lists, free pratique, and port clearance from their previous destination.

Keep these and other documents well organised and backed up by photocopies or stored in the cloud. Have your boat stamp at the ready and maintain the vessel in inspection condition.

While cruising, monitor VHF 16 as a listening channel. Visit the US Coast Guard Navigation Center web page for additional VHF radio channel information.

There you will find a wealth of cruising resources, including links to the frequently updated Local Notice to Mariners available by region.

Another great resource is the National Oceanic and Atmospheric Administration (NOAA) United States Coast Pilot Series.

This free downloadable booklet gives a written summary of all navigation standards, hazards, and highlights throughout the country.

Find the guides online here.

Bareboat Chartering

Bareboat charter requirements vary according to location and company policy.

In general, the US standard is certification from either the American Sailing Association (ASA) or US Sailing.

The ASA bareboat certification is course 104, which can be obtained only after completing the organisation’s basic keelboat and coastal cruising courses.

Be ready to produce a sailing resume with at least 80 hours of experience.

Consult your charter company to find out whether other credentials, such as the International Certification of Competence, are acceptable.

The bottom line is to conduct your research specific to the location you plan to visit.

Regardless of experience or coursework, the decision on whether to rent a boat to you will ultimately be up to the individual charter operator.

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